


A Match Made

by Hannahible



Category: IT (2017), IT - Stephen King
Genre: Blood and Gore, Dominant Pennywise (IT), F/M, Manipulation, Minor Character Death, Oral Sex, Possessive Pennywise (IT), Rough Sex, Slow Build, Stalking, Twisted and Fluffy Feelings, Vaginal Fingering, Vaginal Sex, Violence
Language: English
Status: In-Progress
Published: 2018-02-04
Updated: 2018-02-10
Packaged: 2019-03-13 10:02:51
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 5
Words: 9,143
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13568274
Author URL: https://archiveofourown.org/users/Hannahible/pseuds/Hannahible
Summary: She had no idea that moving to Derry, Maine would change her life so completely. She had no idea she'd be right across from the horror house, the local legend, "THE" house that all this kids whispered about at sleep overs and over camp fires. She didn't know that she would attract the attention of something else or that, after keen observation and subtle experiment that it would decide that it wanted her completely to itself.





	1. The Move In

**Author's Note:**

> Heyo! If you're not a fan of clowns or the pairing of Pennywise and.. anyone, really, then this isn't the place for you. It should be obvious to make this sort of story work that I will have to bend some Pennywise's personality and character a little bit on the occasion and that, due to the nature of Pennywise as a whole, that this wouldn't be considered a conventionally "healthy" relationship.  
> I do want to state early on that I am going to integrate my own theories on Pennywise and his existence and such which does not come till later.  
> There WILL be sex, but we'll get to that when we get to that.

Hannah didn’t think anything was odd about her moving to Derry, Maine. It was a small town, the tiniest little pinpoint on the map and that’s where she decided she were going to move to..

Why would she move to Derry, Maine?

A wonderful question. Aren’t you a bright little bulb in the box?

She decided to move to Derry after a bad break up and by chance Hannah had learned that she had old family ties there that had long since passed, so it was all she had at this point. A small little house on Neibolt Street, number 20 something… Ah yes, a quick glance at the papers mailed to her is all that was needed. Number 26.

The papers mailed to her were documents, explaining the small fortune left to her, the properties, and how after years of searching they found the closest living relative to take charge of the estate which was, you guessed it, Miss Hannah. They found her just in time too, as the state was ready to absorb the estate after no one claimed it for so long. The papers also came with a small postcard.

It was an old timey little thing, and it would make anyone think of the 80’s and one couldn’t help but think that maybe since this was a little town they were a little favorable of, “tradition.” The postcard said, _“Nothing Changes in Sweet Old Derry!”_ and the picture of the town on the postcard had a very vintage feel to it. It was cute though, and since she had nothing tying her down to her life here now since her breakup, she packed up her things, sent notice, and she were to be moving in.

She were quite a drive away, so after a quick phone call she had hired a cleaning, electrical, and plumbing service to come to the house and get it all running, hopefully, by the time she  got there. The reviews on google suggested they were very thorough.

Hannah wasn’t that worried on the condition of the house other than that, as the notice sent to her assured that the house suffered no vandalism or squatting or anything of the sort. That was odd, but she figured it was just the size of the little village.

When she reached the small town, she learned the postcard was right. Nothing had changed in Derry according to that picture. As Hannah drove through town, she could see the bustle of kids and teenagers. Mothers taking groceries home, old men sitting on benches together to talk the daylight away, and old women flocking to boutiques in their silly little hats and handbags in tow.

It was charming. The physical manifestation of a family home town.

But as Hannah drove, she  noticed people noticing her. Herr unrecognizable car, the unfamiliar license plate. It was a close knit community. She chose to pay it no mind, following the directions on her GPS to her new house and when she turned the corner, she knew immediately why her house had remained untouched. Across the street from hers, an old condemned house sat. The wood that had been used to build had rotted black and certain parts even looked burnt and the windows were broken out. The chain link fence had put up no fight to the weeds and long grass that plagued the now dead yard, and her house was the only one directly across from it.

The others had quite a bit of space from hers, giving her own house a decent sized yard. To her utter delight it was a small bungalow style house. It was a mixture of brick and wood, with a small porch, and a second floor that you’d guess had maybe one or two bedrooms and one full bathroom, tops.

In the street she saw two vans parked in front of it and she guessed that they were the service she had called so Hannah pulled into the small driveway, and got out of her car into the toasty warm air that had a gentle breeze to glide across her skin. She closed the car door behind her, her phone and keys shoved into her shorts pockets.

The sound of the door attracted the attention to the temporary inhabitants of her new house, and three people came pouring out. There were two men and one woman. The woman was an older lady, and from the rubber gloves on her hands and her hair pulled back with a scrunchie and bandana, Hannah figured she was the cleaning lady.

The two men she wasn’t able to guess who was the electrician and who was the plumber. One was a little shorter, around five foot seven, and was definitely older with a bit of meat on his bones. The other was a conventionally attractive man with stubble and a baseball cap on.

Looking at them, she suddenly became self aware. Despite the older man being a little bit on the short side, she was definitely shorter, and she were by no means in peak physical condition herself with the extra fat on her thighs, arms, and stomach. She wearing shorts, flip flops, and a short sleeved worn Marvel t-shirt that she had slept in so many times.

She had rubbed her hands on her shorts, beginning to walk up to the house.

“Heyo! I’m the owner of this place, I’m the one who called for your services,” the young woman called.

She flew up the stairs with light steps, coming to a stop in front of the three who had nothing but friendly expressions on.

Baseball Cap guy offered Hannah his hand to shake, which she did, as he spoke. “Hey there, Miss. I’m Carmen Tanner, I’m your plumber. Your pipes are pretty well working, it seems none of the local kids had felt the need to come in and try to pillage any of it. This man beside me here is Ted Ronski, he’s your electrician, and this here is Margretta Ford, your cleaner.”

Hannah offered a small smile to each as he introduced them to her, and when he was finished, she again spoke. “A pleasure to meet you all, you can call me Hannah. Wanna tell me how the wires are an’ all that?”

Mr. Ronski grunted quietly, giving a small nod. His voice was rough, like a smoker of twenty years. “Yer wiring seems all good, Miss. A lil’ outdated which in any other house would be a big ol’ fire hazard but yer house here hasn’t suffered any infestations or leaks that could cause damage to make it a hazard. I highly recommend getting all of that upgraded in the next five years or so, though.”

Miss Margretta Ford picked up after him. “And cleaning is going well. I packed up most of the things left behind in boxes. I’ve been trying to air this place out.”

The shorter female listened to each of them, smiling at the end. “How wonderful! Thank you all very much. I know you’re still probably doing a few checks but..” she gestured to the bed on her car, holding all of her things, “could you help me move some of the bigger things into the house? You don’t need to help me set it up or anything, but I can’t carry it myself..”

Both Mr. Tanner and Mr. Ronski were obliged to help, and Miss Ford was more than happy to do a quick tour of the empty house while they loaded the big appliances onto the front yard first..

For the next two and a half hours the three of them went above and beyond, helping her get her refrigerator, laundry machines, bed stand, mattress, and bigger pieces of furniture set up. It seemed they had a lot of practice doing this, so they were fast. By the time they were done, all she had were boxes to load into the house and they even assisted in stacking those up just inside. Everything was in order and mostly taken care of, so after she paid via credit card, she also added a large tip. She had the small fortune to be able to splurge a little bit now, so why not?

Each of them got a 100$ tip. As they left, Hannah unloaded certain items. She got her binders full of all her dvds and tv show series out onto the tv stand, her boxes of silverware, dishes, cooking utensils, and all of that went on the kitchen counter. Throw pillows and small blankets were tossed on the couch and chairs, toiletry related things were tossed into her personal bathroom, and then after that it just came down to unpacking and organizing. To nesting.

It was late afternoon so she had some time to get most of her bedroom setup, actually. She got her desk setup, her dresser and closet, all of her personal crap, and most importantly, her bed was made. By the time she was done putting everything in the perfect spot, it was about seven o’clock, and it was a friday night. With her keys and phone still in her pocket, she went out, unhooking the bed from her car and driving into the main part of town where she located what looked like the town’s most favorite diner/bar.

She got a lot of looks from the townies. She was an unfamiliar face, she probably smelt sweaty and looked tired as heck. She offered a few small smiles, a few arched brows and unimpressed looks, but for the most part she minded her own business, ordering dinner and filling up for the night before going home with the new mental note to buy groceries.

“Yo’, that’s the out of townie that moved into the place across from Number 29 on Neibolt Street, right?” she heard some slightly tipsy man rudely ask whom one could only assumed was a more sober buddy.

Hannah glanced over, frowning. She instantly became more curious when she noticed the sober man was scowling at his drunk friend.

“Could you possibly have less grace than that?” he hissed, turning to look away from him, and blatantly avoiding looking at the short woman.

She rolled her eyes to herself, done with the food anyway and left quietly after paying, thankfully all with no hassle.

That night, when she collapsed into her bed with her shirt and shorts thrown haphazardly on the floor, she were too tired to even think of turning her head to look out her bedroom window, where across the street at Number 29, a dim light lit up the broken windows for a few minutes as if something was watching the new homeowner. 


	2. A Stranger

**Notes for the Chapter:**

> This update came a bit fast but I already had it written so I figured I'd post it.

The next morning when she got up, Hannah went through her things in order to get the stuff she needed to take a quick shower. In her bathroom she had a large porcelain clawfoot tub with detachable racks and an overhead shower installed above it. Anyone would have loved it. Thankfully there were shower curtains that went completely around the tub, and on the floor surrounding it there were four shower rugs specially made for it.

She took a quick and swift shower that felt amazing because she learned, to her utter pleasure, it had wonderful water pressure.

Hannah wasn’t in there long though because she had a lot to do. She had it written down in a notebook of the list of things she needed to get done so after she was dried off, dressed in today’s clothes and her hair was thrown up in a towel, she sat down at her desk and grabbed the notebook that had been set out on top.

To Do:

-Get Big appliances set up  
-Get wifi set up  
-Get bedroom done  
-bathroom  
-kitchen  
-livingroom  
-check out the basement  
-grocery shopping  


The list went on.

The short woman had a few things done already but one figured grocery shopping would be the easiest to do.

She grabbed the towel on her head and began to scrub her very short hair with it. Afterwards she quickly ran a comb through it to keep it manageable, and finally threw a beanie on top.

For whatever reason, she didn’t mind wet hair and so she prefered to let it air dry.

She slipped on her shoes, grabbed her wallet and keys and she went out.

She located the grocery store pretty quick, and for once Hannah was thankful that since it is such a small town there are only a few limited places one can go to get their groceries and you didn’t have to go far.  


As she rolled her cart through the small grocery store, she listened to the quiet music reminiscent of elevator music playing through the speakers. She grabbed what felt like one of everything. All the basic seasonings, sugar, coffee, condiments. She grabbed meat for the freezer, snacks for snacking, fluids for drinking. Her cart was packed and she couldn’t even bat an eyelash. There were a few ladys with their children in the store with her and she got a few looks that she returned with small smiles.

As the cashier ran her things for her, she felt the back of her neck tingling as if someone was looking at her. Hannah tried to ignore it as she was quickly growing use to staring in this town, but the feeling just kept growing stronger until she couldn’t stand it any longer. She looked up and around, her eyes being drawn to the front windows of the store.

It’s where she felt the eyes but there was no one there. She shuddered wondering why in the hell she got this feeling if no one was looking at her but her only option was to write it off as nerves.

“247.68 dollars, ma’am” the cashier said. She handed over her card which they swiped, and grabbed her cart that was now full of grocery bags and went out to her car. As she was loading things up into her car, the backseats and the trunk, she felt something light smack into her.

It made her jump, and so she looked. The breeze had blown a poster into her leg. She thought it odd because she hadn’t noticed any wind earlier today, but she grabbed the paper, lifting it to look at it.

It was a Derry Poster, promoting their annual festival.

‘I didn’t know they had one of those’ she thought to herself, closing the trunk as she looked it over. It was going to be there in a few days. She folded it up neatly and put it in her pocket before gently pushing her cart back into place and climbing into her car to drive home.

When she was driving down her street, for whatever reason she glanced over at the creepy house across from hers. Her eyes widened.

She saw a tall figure in the backyard. Tall, and the only colors she caught were red and white. She slammed on the breaks and backed up, trying to see who on earth the person was and why they were standing in the backyard of such a creepy house but there was no one.

Maybe a trick of the light?

Hannah exhaled slowly through her lips, returning to getting to her house so she could get it set up and she shook off the weird experience. By the end of the day she had gotten a huge amount of progress done and since it was only a saturday, she figured why not go out and get to know some of the locals. She ended up taking another shower and got ready before returning to the little diner/bar she visited the night before.

This time she ordered a drink and hung out at the bar, where not soon after she was interrupted by a townie just as she hoped she would be.

Hannah felt a gentle tap on her shoulder, and she turned around until her breath got caught in her throat.

Before her stood a very tall man. Very tall with chocolate brown hair, sharp cheekbones, and light grey or blue eyes that pierced right through her. He wore a black sweater that had the slightest bit of a turtleneck and black jeans that hugged his legs. Legs that went on for ages.. He did not look like a small town kind of man.

“I.. Y..yes?” she stuttered, mentally slapping herself for sounding like an idiot.

She saw a small quirk on the man’s lips.

“You’re new, and I thought I’d greet you to Derry. Your name is Hannah,, right? I helped put together the documents sent to you,” he spoke. He had a soft lower voice, that was just as chocolatey as his hair color. He offered a hand, long nimble fingers extended out towards her.

She was caught off guard. She didn’t know whether to freak out or just go with the flow, she was caught in a little bit of a whirlwind.

“Ah.. Yes, I’m Hannah,” she slipped her much smaller and less graceful looking hand in his, letting him lift it to his mouth where he brushed his lips over her knuckles.

She wanted to arch a brow and say, ‘really?” but she restrained herself for she didn’t want to appear rude on her first impression. Besides, it was kind of sweet..

“Have you been getting settled in well? No problems?”

“No, none at all. I’ve actually been getting a lot done very quickly, actually,” she relaxed, comfortable with the noninvasive small talk.

“That’s good. I was afraid I was going to have to offer my assistance,” the man offered a small smirk, and she returned it with a small laugh, a small shiver going up her spine. Something was off about this man.

“No worries there then, I got it handled.”

The man nodded, running a critical eye over her.

Why did the people in this town have such a staring problem?!

She became self aware again, quickly becoming uncomfortable. She was wearing a cute navy colored see-through shirt that she wore a sports bra on underneath and then she had high rise black shorts on, paired a neat pair of combat boots. She looked good. She was a bigger girl but that only added to the simple look, however she suddenly felt very naked in front of him. Like he was seeing through her.

“Well,” he suddenly spoke, turning away for a second, a small gesture, “I better get going. I have some things to take care of but, everyone here in town is talking about you. They want to know what lady had the courage to move in across of our local campfire scary story legend, isn’t that right, everyone?”

A sudden surge of men and women yelled in agreement, and she finally realized most of the people in the diner had been listening in on her conversation.

‘Nosey bastards, then, aren’t they?’ she thought, and she heard a slight snort escape the man’s throat. Hannah stared up at him, wide eyed, assuming that he was laughing at something else because she definitely didn’t say that outloud.

They all seemed familiar of the man in front of her though.

“Have you lived here most of your life?” she asked, unable to stop the question from pouring out.

A large grin spread across his face, and he said slowly, “I show up every couple years or so.. People tend to think they know me in Derry even if they have never met me.”

It was a strange reply. How does that even work?

“Must be one of those faces,” he continued, the smile still on his face. It was like he was in on a secret that no one else knew about.

“I really must be going now, though.”

The shorter woman jumped, realizing she completely ignored the fact that he said he had to go.

“Oh! Right, yes. You better go. But I didn’t catch your name?”

“You can call me Robert Gray,” he almost purred the name before disappearing into the crowd, and she was left to the rest of her night.

**Notes for the Chapter:**

> Please don't forget to leave a comment and support for this story! I like to know that you like it.


	3. Night One of Derry Festival

**Notes for the Chapter:**

> Just want to remind that this is a slow build up to the sex, lol. This isn't porn without plot. It's definitely got a lot of plot.

A few days had passed since Hannah had met the very strange and very tall Mr. Robert Gray. She couldn’t say she thought very often of him over the course of the next few days, and she couldn’t say she wasn’t completely disinterested in him either.

Men who looked like that didn’t speak to girls that looked like her. IT peaked her curiosity.

Over the past few days she had finished nesting in her house, and that was with a great deal of assistance of the local stores. She had a few items she had forgotten she had left behind, like a broom, a vacuum, a mop and bucket. All of those kind of cleaning agents she had forgotten.

Every time she had went out she had ended up meeting another local. Many of them just watched her from a distance, not having the nerve to introduce themselves, but there were a few.

She became quickly acquainted with the cashiers at the stores, finding out their ages, and even

the names of their parents, because of course people liked to talk within earshot.

She figured out if they went to school or if they ran with, “that one group of boys.”

She learned that some woman here in town was having an affair and that some men were back on the market.

It was interesting to say the least, how such small towns will create drama when there is none to be entertained by.

But today was Derry’s festival. Hannah had ended up pinning the poster to a board she had hung up in the kitchen, and she memorized all the information. She didn’t even have to set up her GPS, because as she had been driving around for the last few days she had seen carnival rides, tents, booths, game stations, and the like all being set up in the center of downtown.

It was the first day of the festival, and she decided she was going to check it out. Maybe eat some candy, ride a ride, play a game or two. It would be good to get out and have some innocent fun.

So, an hour or so before sundown, she got ready and went out. All she had on was a simple tshirt, jeans, and a flannel jacket. There was no point in dressing up for today.

As soon as she was within two blocks she could smell it. The cotton candy, the popcorn, the hot dogs. It filled her nose and she relaxed. This was a familiar place to her.

When she entered, she could hear the yells, the screams, the laughter. Games going off, pins falling, children everywhere. She loved it and she immediately felt right at home.

A little while in, the night had fallen and the area was lit up by strung lights everywhere. She hadn’t ate or gotten anything to drink yet, so she decided to get a soda.

She paid the kind old man at the booth she had gotten it from and turned around, only to run into Mister Tall, dark, and handsome himself.

She jumped, almost dropping her fresh drink, “Jesus!” and she groaned to herself as she realized who was in front of her. Making a fool of herself again.

“I didn’t mean to scare you there, but I saw you were alone and figured I’d offer to join you,” Mister Gray intoned, sounding amused and when she looked up she could see his apology was completely insincere. He had fun getting a scare out of her.

“Rude.. “ she sighed before brushing the harmless scare off and smiling. “I have no reason to refuse, I suppose. What’s up?”

The man arched a brow at her and repeated back slowly, “What’s… up.. Very informal, aren’t you? Well, to answer your question, I have been quite well. I had the most wonderful dinner the other night. Yourself?” They began to walk through the festival, looking over the booths and stands as they spoke.

She batted her hand in a dismissive gesture, “Same old, same old. Everyone in this town has a staring problem. I don’t understand what their deal is.”

Robert Gray smirked, the same one as last time. As if he was in on a secret no one else knew about.. “As I said last time. They’re curious. You moved into the house right across from Derry’s very own local legend. Every town has one.”

“Yeah, yeah, but I don’t get it. I don’t know the legend, how am I supposed to know?”

“So, no one has told you yet.. How charming. I guess I get to do the honors.”

“Oh yippee,” she rolled her eyes, scoffing slightly. “I fail to see how this legend is such a big deal. “

The man hummed in the back of his throat. He seemed very amused but Hannah couldn’t for the sake of her figure out why.

“Look there,” he spoke, pointing between booths to a little alleyway that was illuminated by the cast off light of the festival. “Do you see that mural?”

Hannah narrowed her eyes on it, making out the chipped paint on the brick. “I guess?”

Mister Gray took a few steps towards it. The steps were almost skips, he seemed very excited to show her, but his legs were too long, steps to large, for it to be any more than a slight spring in his step.. When she looked at his eyes, she noted that they looked a bit brighter than usual. More blue than the first time she met him. Must of been the lighting.

She followed cautiously, just enough that she could make it out relatively clearly.“Yes, I can see it now.”

Mister Gray suddenly leaned down, wrapping his arm around her shoulders and pulling her close into his side. He ignored the clear uncomfortable body language she was giving off at this action and he pointed again. “You see that painted car? Look near the back tire..”

Hannah hesitated, but she slowly dragged her gaze to the area he was telling her to look. She suddenly felt a wave of dizziness hit her like her blood sugar dropped, but she had just gotten a soda so she knew it wasn’t that. Then her eyes locked on it.

‘Holy heck,’ she thought. Right there, under the car was the face of a clown. A clown that didn’t look entirely human. There was something off. It’s head was very large. It’s eyes were yellow and it’s face was painted white. The paint on the mural was so old she couldn’t tell if it was the paint chipping or if the “face paint” was actually supposed to look chipped, but it added to the unnatural vibe it gave off. The nose was painted red, along with it’s lips and lines connected the corners of it’s mouth to up above it’s eyes. She was steadily creeped out until she saw it’s face turn towards her. The painting fucking moved! She could feel her heart start beating hard, her breath quicken, and she could swear she could taste blood in her mouth. That sort of thing only happened in movies, so why on earth was it happening in front of her in real life?!

If she focussed, she could of sworn she heard children singing down the alleyway and then the painting of the clown moved again. Like it was climbing out from underneath the car to stand next to the mural. Long gangly limbs were everywhere, twisting in unnatural ways, and she saw it laugh as it stood up. On the wind she could of sworn she heard it. An almost childish giggle. It stood straight up, and it had to be at least seven feet tall in pure height alone, not counting the wild firey hair. It lifted one gloved hand up, giving a small wave with a smile on it’s face.

She was suddenly josted and she yelped, full body flinching and she blinked. The clown was back in it’s spot on the mural, and she was still standing next to Mister Gray who had his arm around her.

“Are you alright?” he asked slowly.

Hannah took a slow shaky breath, glancing around the alley and her surroundings before looking at him. She could still taste the metallic tang on her tongue, could hear her heartbeat in her ears.

“Y..yeah, I’m fine. I just thought I saw something.. Anyway, you were saying?”

“Well, you saw the clown painted underneath that car, yes?” he hummed, leading her away from the area to continue their stroll through the carnival. Hannah instantly felt more at ease facing bright lights, people, and laughter filling the air.

“I did. “

“Well, this town has a history. Lots of catastrophes, deaths, missing persons, ever since the settling of this place. The police either never solve the crimes or they simply pin it on someone, but a string of missing children happen every couple of years. You read in the paper how a kid went missing a few nights ago, yes?”

Hannah blinked, confused before light dawning in her eyes. “Oh, I haven’t started paying for my paper yet, I was planning on getting that taken care of tomorrow, so no.”

Mister Gray nodded, seeming a little disappointed at that fact. An odd thing to be disappointed about.

“Well, the children in this town believe something is causing all this mayhem. Something not entirely.. Human.. Years ago, when settlers found this place, they all ended up missing. The people thought it was the Native Americans, that they had attacked but… none of them were found either. All that was found was a pile of bloody clothes near an old well. All the plants and fauna surrounding that well was dead, too. See, the thing is, these kids all grow up and they seem to forget these little tales and learn to think of them as campfire stories, but that childhood fear is always rooted in their very core.”

Hannah looked thoroughly unimpressed. “Really? So they think a big ol’ scary clown is coming to murder them?”

Mister Gray laughed, glancing down at her. “In a way…”

“Well, if these kids grow up and ‘forget’ how do you know?”

“I like to watch. I listen. I have been very… invested within the history of this place. It’s… fascinating.”

“Well, that might be, but how does this involve Number 29, Neibolt Street?”

Hannah watched the same light from earlier fill Mister Gray’s eyes again. If she let herself believe, she could of sworn there were actual lights floating behind his eyes. A large grin spread out across his face, and then he cackled. It was a strange one, as if it didn’t belong to him. It caused an uncomfortable shiver to run down her neck.. “Asking the right questions, I see! The well is where some of these local kids believe this monster resides. And number 29 was built right.. Over.. it,” he purred, putting emphasis on the last three words.

It felt like a bucket of ice cold water was just poured over her. She felt a creeping fear trickle up her throat, reminiscent of when she was a child watching horror movies she was told she wasn’t allowed to but watched anyway when her parents weren’t home. She didn’t know why she felt this way. It was like her emotions were out of her control.

“They’re just stories, of course!” Mister Gray’s voice suddenly ripped her out of her thoughts.

“Who would really believe a big baddie Clown would be coming after the children?” he said, like he was making fun of the idea, but there was a dark lilt to his voice.

“You never know..” Hannah murmured quietly and Mister Gray suddenly went very quiet. She was mostly just thinking out loud, but the more the thought formed the more she felt the need to share. “A monster like that could exist. We know about space than we do our own oceans, so it could be real. Taking on the form of a clown, taking the children. But a monster like that is akin to a wild animal. I couldn’t imagine that it would just be taking the children. Animals only want two things. To eat and to mate. If it was real, I’d say it’s just eating the children.”

“And the mating aspect?” he said slowly.

“Maybe it just hasn’t found it’s mate yet.”

“Maybe…” he repeated quietly.

**Notes for the Chapter:**

> Please don't forget to drop a comment and a kudos! I want to know what you think and if you like it!


	4. Surprise Appearance!

**Notes for the Chapter:**

> This chapter is a little bit shorter than the others, I know, and I'm sorry for that but I was a little bit crunched for time. I hope you enjoy it anyway!!

Hannah had a shaky night at the festival. She managed to act normal after… that happened.

Her mind flashed back to the clown clawing out from underneath the painted car, like it’s long limbs were broken at the joints and it just couldn’t feel the pain.

A shudder of moderate disgust ran down her spine.

Maybe she was becoming overwhelmed, on the edge of a mind break. Maybe she was getting a fever.

The break up, the move, the staring and creepy house. It all had to be taking it’s toll on her.

The festival normally went on for about three days, but she didn’t think she’d go tonight.

Last night was pretty eventful for her and she figured that maybe if she was getting a fever that it would explain her hallucination of that clown last night.

She didn’t know how she felt about Mister Gray.

When she was around him she couldn’t deny that he was an odd character. He seemed cool and nonchalant one moment, mysterious the next, childish at other times, and even slightly wild. She could almost see it underneath his skin.

She recalled the odd cackle that escaped his throat. It gave her shivers just thinking about it.

It sounded so foreign, like he was an entirely different person with a voice much more squeaky than his own.

He also had no sense of personal boundaries, throwing his arm around her shoulders and pulling her close like that. As if they were an item.

He was odd.

But she liked it. She liked being around a more eccentric person. It’s not often she gets to meet one after all, though normally, back where she is from, she is the one considered eccentric.

She didn’t think people normally referred to Mister Gray as eccentric but it was the only word that relatively fit.

She had a job just outside Derry at a hotel a few miles off and other than that, she had no plans aside from staying in, taking a shower and going to bed.

She was both a cleaning lady and one of the front desk workers. She didn’t mind, it kept her busy in the small hotel that many didn’t seem to visit.

While she was working and she hit her break, she decided to go to one of the unused rooms to take a nap on one of the beds. Because there weren’t many visitors the bedding was practically brand new and rarely ever used. Rarely any chance of bed bugs or any other infestations.

As she laid down on one of the queen sized beds, she groaned as her body ached intently before relaxing.

She slid her phone out of her pocket, setting the ten minute alarm and then she closed her eyes. Then immediately opened them again.

‘What was that?” she thought, her breath shallowly escaping her chest. She heard a sound.

A ta-ta-ta-tap, like when someone clicked their fingernails on a desk or wall. She stayed still, and she tensed when she heard it again. She slowly sat up, looking at the bathroom where it came from.

Ta-ta-ta-tap.

There it was again. Hannah took slow quiet steps towards the bathroom, mentally praying that it was just a rat or something that got stuck.

It was a foolish thought, but one she entertained regardless.

Ta-ta-ta-tap

Again. She stopped right in front of the bathroom, and flipped the switch on the outside that turned on the lights inside. She gave a few seconds.

Ta-ta-ta-tap.

She grabbed the doorknob carefully before wrenching the door open, her body tense and ready the freak.

But there was nothing. There was no one in there. No bugs, no mice or rats, no person. It was empty.

She sighed, shaking her head, closing the door again, and flipping off the switch she turned around only to jump back, a scream stuck in her throat and a strangle gurgling sound escaped her instead.

The clown she hallucinated before was right in front of her. Her back slammed up against the bathroom door, and she made the sound again.

The clown didn’t move. But it certainly drooled. A large smile on it’s face as it stared down at

her.

“W..what…” she breathed out, her voice tight. The clown leaned in close, ignoring as Hannah slid down the door to try and get away. It just bent down, not letting her escape.

“Boo!” it whispered before roaring with laughter at the small flinch it got out of her.

In her fear, Hannah had a small burst of courage and she swung, smacking it’s face hard with an open palm as it laughed.

When her palm made contact, a sharp crack resonated through the room as it’s laughter cut off.

The clown suddenly lost it’s smile and it’s yellow eyes darkened. It’s expression was one of a wild animal. It clicked it’s tongue, wagging a finger.

“That’s very rude, Hannah. Don’t raise your hand to me. Bad decision, bad decision, bad decision, bad, bad, bad, Hannah. Very bad..” It’s voice was odd, rough and low one second and high and squeaky the next. Sometimes the two sounds blended together to make a very strange sound.

“Maybe I was wrong about you,” it continued, and she honest to god could not care to bother trying to figure out what that means. If this was a hallucination, it was fucking terrifying!

A small surge of fear wracked her body, and she swallowed, recognizing her body’s reaction. She had a strange, but not wholly uncommon reaction to fear. The adrenaline, the terror. It confused her body, resulting in a familiar tingling signifying arousal.

It inhaled sharply, it’s eyes rolling back in it’s head completely and then a large grin spread across it’s face again.

“Then again… maybe not.”

Hannah squeaked, squeezing her eyes shut. She heard it giggle and when she opened her eyes again, it was gone. She exhaled heavily, glancing around the room. It was empty. She placed her palm to her forehead, swallowing hard.

‘The absolute fuck…’ she thought to herself. She stood up on shaky legs, no longer feeling the need for a nap and she went back to work.

Later that night when she was home, she ended up curled up on the couch under a blanket, watching movies. She had a bag of popcorn, and she a large bottle of water with her.

She figured her episodes as of late were of concern so that night she decided to kick back and relax. Before she did though she happened to look at the paper she was now getting, and she couldn’t help but notice that there seemed to be a lot of missing kids in this town...

**Notes for the Chapter:**

> Please don't forget to comment and kudos! I want to hear your guy's theories, your thoughts and such. I love them.


	5. Third Night is Full of Pleasures

**Notes for the Chapter:**

> Here it is! Finally a taste of some of that more filthy content you've been waiting for, but alas, it is just a taste, another torment for our main character, another experiment from our dear clown!  
> I hope you enjoy it, as It did get a little bit away from me as I was writing it.. I am going to have to take care of myself after posting it, it ahh... definitely got to me. Enjoy!

The third day of Derry Festival, Hannah still didn’t really want to go out. She couldn't tell if she felt better or not, because honestly she hadn't felt sick in the first place. Strangely enough, the two hallucinations hadn’t had a huge effect on her other than the temporary fright she had experienced.

She didn’t feel the need to look over her shoulder and keep all the lights on. In fact, the only lingering effect from the incidents was the tingling sensation between her thighs. Personally, she believed her reaction was because she trained herself to be that way to overcome childhood fears.

If you find it desirable you can’t be consumed with fear, right? Since then she has always had a strange thing for clowns and monsters alike.

She found romance in the most twisted representations on tv, and she ached for the villains. She kept these feelings to herself, though. She knew they weren’t considered “normal” or “healthy.”

A quick check in her fridge proved she was out of a few things, so she grabbed her keys and headed to the grocery store.

She was dressed rather lazily, but she wasn’t going to be out for long so she didn’t care.

She did care, though, that she ran into Mister Gray at the store.

She turned the corner and there he was, awkwardly holding a bag of chips and reading the ingredients.

“Are you just stalking me or is the fact that this is a really small town prevalent as to why I keep running into you?” she said, one hand on her hip, the other holding a basket, and her eyes trained on his face.

Mister Gray looked up, still holding the bag of chips. His expression was slightly confused but he quickly came into focus as soon as he realized who she was. His gaze relaxed, and his eyes trailed down her body and back up again.

“I imagine that it’s just the small town, Miss Hannah,” he intoned, setting the chips down.

“If you happened to drop by the festival last night, I’m sorry that I couldn’t join you. I was caught up in… other matters,” he added, carefully stifling a grin.

“I didn’t go, anyway. I thought I was starting to get a fever so I stayed in.”

“Well, are you going tonight?” he began to follow her throughout the store as she began selecting her items.

She scoffed gently. “Most certainly not. I didn’t even realize I was getting sick in the first place.”

“But it’s the last night!” Mister Gray looked positively scandalized.

“And?” Hannah arched a brow.

“The last night is the best night. We have fireworks, shows have their grand finales. Kids sneak out of their bedroom windows to go, you can’t miss the last night!”

Hannah frowned, pausing. “So? I have no idea how this whole thing works.”

“Well, I can take you!”

She laughed, looking up at him. “You will take me? Like, what, on a date?”

Mister Gray furrowed his brows, and she was struck again about how handsome this strange man really was. “If that’s how you’d like to look at it.”

Her amusement got stuck in her throat, like a bad pill she had to swallow. “I.. guess. You know where I live, right?”

Mister Gray smiled. “Everyone does. I’ll swing by at six.”

“Six,” she repeated, and watched as Mister Gray left. It had completely escaped her notice that he didn’t even buy anything.

Later that night, she had barely finished getting ready by the time she heard a knock at her door.

She shoved shoes on before going down the stairs in a quick little trot, and then she opened the door.

Mister Gray was standing there, looking rather good as he always did, and she offered a small smile.

“I’m here… as you can see”

Hannah laughed softly, grabbing her jacket. “Yeah I see that. Let’s head out.”

And they did. But, instead of taking a car or anything, they had decided to walk. Hannah hadn’t bothered to notice whether or not there was another car parked in her driveway. When they got to the festival, she didn’t notice a large difference in the amount of people there than on the first night. She had thought the first night was already pretty packed but it was nothing like tonight. The entire town had to be there.

They ended up actually participating in the booths this time, playing games and going on rides. The conversation remained mostly light hearted and if anything weird happened or was said, it was brushed off without a single car. At one game stand, Mister Gray even won her a large stuffed bear. Literally massive, it was as tall as her. Robert had ended up wearing it on his shoulders as they waltz around the area.

A few dark jokes were slipped here and there, and Hannah wasn’t afraid to say she enjoyed it or even joined in. In fact, a few times she felt her laughter turned into a more menacing cackle of her own, but lets not choose to dally on that, shall we.

Nearing about eleven at night, Mister Gray grasped her hand, pulling her aside into an alley. He had her hold onto the bear, and with his long limbs, he pulled the ladder of a fire escape down.

Laughing, she followed him up onto the roof, where he very goofily sat down and then patted the spot next to him.

Hannah gently set the bear down beside them as she sat down.

“Why are we up here?” she asked, slightly out of breath.

“The fireworks! Why stand in a crowd full of people when we can watch them easily up here?”

Hannah nodded, agreeing with the sentiment and then they waited quietly until all the lights in town were powered down. All the chatter going down below turned into a small hum. After a few seconds, the fireworks began to off.

Hannah was watching in awe. The thing is, they were in Maine. They were high up. The lights were turned off, and from the way they were facing to watch the fireworks, behind them she could even see the Northern Lights.

It was beautiful.

It took a little bit of a dark turn when the fireworks seemed to form into a face before her very eyes. A familiar white face with yellow eyes and a red smile. She shook her head, frowning, and soon everything was back to normal. Regular fireworks, a pleasant night.

The comforting buzz of conversation and gasps and laughter down below. It was a nice night.

All too soon the night was over, and Mister Gray was wisking her off home.

They chattered and talked as he walked her home in the dark. Many people were on the streets tonight, very few bothering to take a car out.

It was nice.

When they walked up her porch, she turned to him and offered a bright smile as he again handed her the large stuffed animal.

“Thank you for convincing me to come out tonight. It was a lot of fun.”

Mister Gray smirked back, glancing up before dragging them back down to her.

“Don’t worry about it. It’s not often I am able to ease someone so easily into my more.. Darker humour. You made it a memorable night.” He had an odd look on his face, and Hannah got the feeling he had never “eased someone into his darker humour.” She got the distinct feeling she was the first, and when she tried to take a few mental guesses as the were that was, she got the feeling she wasn’t going to like the answer. There was no doubt in her mind that he was a dangerous man.

“Well, It’s late. I better get to bed.”

“Yes, you better scuttle up to your bedroom. Goodnight.”

“Goodnight!” With a small wave, he descended her stares and she entered her house. The lights were off and she was feeling good.

She shrugged off her jacket, and kicked off her shoes, grabbing the large stuffed animal and climbing the stairs to get to her bedroom. When she entered her room, she turned on a small dim desk lamp because she didn’t want the harsh overhead lights on right that moment. She laid the large stuffed animal across her bed, beginning to take her clothes off for bed. She only slept in a pair of panties.

She was relaxed, her mind at ease until she heard a slight jingle of bells.

Her body hair rose as goosebumps draped across her body, and she glanced around her room. Nothing.

Maybe it was her imagination. She had distinct recollections of when she was a child home alone and she thought she heard her mother or her aunt call out, but there was noone there.

Maybe it was the same thing. She walked over to her bed, glancing out the window to the house across the street.

‘I wonder why people are so intent on believing an old legend..’ she wondered.

“Maybe because it isn’t a legend,” a dark voice giggles behind her, and she gasps. She instantly recognized that voice. She moved to whip around, but a large hand slammed on her back, pushing her down onto of the bear. The hand pressed down, pinning her on top of it. She couldn’t sit up, couldn’t move. With a sudden realization, she realized she was mostly naked. She could feel her nipples being caressed by the soft fake fur of the stuffed animal. She had forgotten when she heard that voice talk.

That weight pinning her down was no hallucination. “H..how did you get inside my house?”

She heard a giggle and then she could feel him lean over her. “Penny doesn’t need a door or a window. Pennywise only needs to want to.”

He dragged his other hand up her leg, causing shivers to wrack her body. She heard him growl, and she felt something wet hit her back. She grunted, struggling to try and push up. She planted her legs on either side of the teddy bear, and placed her palms on its chest and tried to push up.

“Ah, ahah! Bad Hannah. You aren’t going anywhere away from dear ol’ Pennywise” near the end of his sentence, his strange voice dropped into a low gurgling growl and he pushed down harder, keeping her pinned down.

“Get off of me!” she yelled, and then she hissed harshly through her teeth when she felt a sting on her asscheek. He spanked her! Hard!

“What Penny wants, Penny gets… be a good girl for Penny. He might eat you up!”

She felt him learn down, rumbling in her ear before she felt him grip onto the edge of her panties and rip them off. She gasped, shivering as she felt the cool air hit her embarrassingly damp folds.

She felt, more than heard, him growl in approval. She knew the way that as was spread out on the teddy bear that it was parting her open a bit, giving a peek to the pink flesh.

She felt more of that wet fluid hit her back, closer to her ass this time and she tried to close her legs but she was swiftly punished with another hard crack on her ass.

“Tch, tch, don’t even try.”

She felt something soft, like fabric, land on her leg and then slide down, and then she felt it.

Bare, surprisingly warm but very large fingers run up her inner thigh. She squeaked, her face turning bright red as he pressed his fingers down on her clit.

“So wet for Penny…” she heard him growl, and then without warning she felt two fingers push inside of her. She bit her lip, silencing herself but she heard him snarl and suddenly she felt the hand that was pressing on her back, tangled in her hair, pulling her head back.

“DON’T MUFFLE YOUR SCREAMS FOR ME!” he roared. It almost shocked Hannah, that he would have such an angry reaction, the sound causing her ears to ring, and then she felt it. He began to pump his fingers in and out of her. Forcing them in over and over at a very fast and rough pace. He was trying to get sounds out of her now.

She whimpered as he pressed his fingers down against all the right places. He was punishing her, she could of sworn.

“Don’t you love how your pussy swallows my fingers up? Such a dirty girl, I bet you’re aching for something else..” he rumbled, and she moaned loudly. She felt him pause, and a third finger joined the first two. Three of this monster’s fingers were about the size of an average man’s cock. She was getting her pussy fucked, spread out on the sweet teddy bear that Mister Gray had won for her.

“You’re loving this aren’t you? Loving Pennywise’s fingers inside your tight wet pussy. Loving that you’re getting finger fucked on top of this stuffed toy.” She felt the wet fluid hit her again, but this time between her ass cheeks. She felt it leak down between them onto her hot wet cunt.

He didn’t slow down, in fact, he just pressed his thumb against her clit and she cried out, her body tightening around his fingers. She was so close to cumming.

“Not yet!” he snarled. Ripping his fingers out of her causing a keening whine to escape her throat.

He cracked another one on her ass, and she knew she was going to have red marks.

He leaned his entire body over her, pushing her head into the toy as he began to whisper in her ear.

“Everytime you lay down in this bed… every time you look at this toy, or you think of how that fine Mister Gray won it for you.. I want you to think about how I, Pennywise, forced you to cum all over it..”

Goosebumps ran over her body and she flinched when he suddenly moved. His hand was still forcing her head down, still keeping her in this position and then she went extremely tense. His tongue was pressing against her clit. He was going to eat her out!

She felt him growl again, and then his tongue was forced inside of her pussy. It was long and thick. He could twist it in so many ways, rub against all her good spots while his lower lip rubbed against her clit. He was driving her mad.

She couldn’t stop the desperate sounds of pleasure escaping her mouth, or stop her hips from pressing back against his face. He snarled into her flesh, turning his head this way and that while his tongue remained buried in her. HIt didn’t take more than a few minutes before she was cumming on his tongue, yelling his name. Her body shook with one of the most powerful orgasms that ever wracked her body, and then she passed out.

When she woke up in the morning she would still be spread out on the bear, naked. And she would move her hand down to feel his thick saliva was still coating her, and she wouldn’t be able to stop herself from rubbing her clit to a second climax, feeling like a filthy slut and loving it.

**Notes for the Chapter:**

> Please don't forget to comment and kudos! This was a really fun chapter and I hope you agree. I want to know what you think.


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